Veratraldehyde → HCID 76168090, compound

HRID 597715Notes

Reaction equation

HRID 597715 reaction equation
[C:1]([C:4]1[C:5](=[O:15])[O:6][C:7]([OH:14])=[C:8]([C:11](=[O:13])[CH3:12])[C:9]=1[OH:10])(=[O:3])[CH3:2].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH:21]=O.[CH3:28][O:29][C:30]1[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=O>>[C:11]([C:8]1[C:7](=[O:14])[O:6][C:5](=[O:15])[CH:4]([C:1](=[O:3])[CH:2]=[CH:21][C:20]2[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:18]([O:17][CH3:16])[CH:19]=2)[C:9]=1[OH:10])(=[O:13])[CH3:12].[C:11]([C:8]1[C:7](=[O:14])[O:6][C:5](=[O:15])[CH:4]([C:1](=[O:3])[CH:2]=[CH:32][C:31]2[CH:34]=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:30]=2[O:29][CH3:28])[C:9]=1[OH:10])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 8419VeratraldehydeHCID 665812,3-DimethoxybenzaldehydeHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 2

HCID 76168090HCID 76168090, compoundHCID 76173922HCID 76173922, compound

Procedure

Similarly, equimolar amounts of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one and 3,4-dimethoxybenzaldehyde or 2,3-dimethoxybenzaldehyde are reacted as above to yield the products, 5-acetyl-3-(3,4-dimethoxycinnamoyl)-4-hydroxy-2H-pyran-2,6(3H)-dione, m.p. 223°-225° C., and 5-acetyl-3-(2,3-dimethoxycinnamoyl)-4-hydroxy-2H-pyran-2,6(3H)-dione, m.p. 175°-176° C., respectively.

Sources & evidence

ORD record
ord-9ea04dc2b7594648a1dae420fbf66e65
Source dataset
uspto-grants-1977_03
Patent number
US04015009

Reaction notes

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